A CONVENIENT ROUTE TO 3'-DEOXY-ALPHA-L-AP IONUCLEOSIDES AND 3'-DEOXY-BETA-D-APIONUCLEOSIDES

Authors
HAMMERSCHMIDT F OHLER E POLSTERER JP ZBIRAL E BALZARINI J DECLERCQ E
Citation
F. Hammerschmidt et al., A CONVENIENT ROUTE TO 3'-DEOXY-ALPHA-L-AP IONUCLEOSIDES AND 3'-DEOXY-BETA-D-APIONUCLEOSIDES, Liebigs Annalen, (3), 1995, pp. 559-565
Citations number
25
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
3
Year of publication
1995
Pages
559 - 565
Database
ISI
SICI code
0947-3440(1995):3<559:ACRT3I>2.0.ZU;2-K
Abstract
The cyclic thionocarbonate 3, easily available in three steps from enz oyl-2,3-O-isopropylidene-D-apio-beta-D-furanose (1), is deoxygenated w ith n-Bu(3)SnH to yield the 3'-deoxy epimers 4 [methyl loxymethyl)-3-d eoxy-alpha-L-threo-tetrofuranoside] and 6 [methyl xymethyl)-3-deoxy-be ta-D-erythro-tetrofuranoside]. These are separated by chromatography a nd further converted to the 3'-deoxy-alpha-L-apionucleosides 11-13, an d the 3'-deoxy-beta-D-apionucleosides 17-19, respectively.